Iodinated sulfonamide



Patented Jan. 17, 1950 I *UNI'TED STATE s PATENT OFFICE 2,499,,930 VIODINATED SULFONAMIDE Ramon de Montaner, Barcelona, Spain No Drawing. Original application March 9, 1944,

Serial No. tion November 1 Claim.

As pointed out in the parent application, a characteristic feature of the aforesaid new compound of the present invention is its high therapeutic activity and concomitant low toxicity.

A preferred method of preparing the said new compound of the present invention involves the reaction between a sulfamidic compound, such as p-aminobenzene sulfonamide or any of its halogenated derivatives, e. g. p-aminobenzene sulfo-chloride, with iodine or an iodinated compound, it being possible to use advantageously those iodinated derivatives which result from the introduction of iodine into a benzene nucleus.

According to the present invention, the iodinated compound to be combined with the sulfamide may also contain an amino group; thus, for

example, p-iodoaniline may be employed. Use

may also be made in this regard of a benzene sulfo-halide which contains in para position a substituent which is convertible into an amino group, as well as an iodinated compound which contains an amino group.

The iodinated compound, for example p-iodoaniline, may be prepared as follows:

Nitration HNO;

NH.CO.HC5 NH.C 0.CHa Acetanilide p-Nitro-acetanilide l Saponiflcation Diazotization NaN 0 g-l-H Cl N=NOl NH;

Diazonium salt p-Nitraniline Iodination l I N 0 3 NH! Reduction Sn H01 p-Nitro iodoanillne p-Iodoaniline 525,780, Divided and this applica- 26, 1948, Serial No. 92,221. In Spain March 12, 1943 The following illustrative example sets forth in detail a preferred embodiment of the invention, starting from a benzene sulfo-halide:

Equal parts of p-acetylaminobenzene sulfochloride and p-iodoaniline are dissolved in a suitable solvent, the solution being stirred and heated until the reaction is completed. As a result of this reaction, p-acetylamino-benzene sulfonamido p-iodobenzene is formed, and this is separated by precipitation:

S0101 NHa I TH. C O.OH9 I NH. O O. CHI

p-Acetylaminop-Iodop-Acetylaminobenzene benzene sulfoaniline sulfonamido-p-iodobenzene chloride soup-1G1 N p-Aminobenzene sulfonamido-p-iodobcnzene Similarly, the sodium salt SOINH NH: I

is obtained by the introduction of the -SOaNa group into the molecule, these compounds being characterized by their notable therapeutic properties, as they are perfectly tolerated by the human organismand have absolutely no poisonous properties.

The foregoing example is wholly exemplary in character and it will be understood that there may be introduced also those variations of detail or execution which do not alter the essential characteristics of the invention.

Having thus disclosed the invention, what is claimed is:

The compound of the formula RAMON DE MONTANER.

(References on following page) OTHER REFERENCES REFERENCES CITED 0 Northey: Chemical Reviews, vol. '27 (194 The following references are of record in the pp 147, 148, 188 and 189 file of this patent: Long et aL: J. Am. Chem. 800., vol. 63, June TENT 1941, page 1587. UNITED STATES PA s Marchant et a].: Can. J. Research, vol. 203 Number Name Date (1942) 6 and 8 1 8, 1 Northey: The Sulfonamides and Allied Com- 91 Behmsch 1 4 pounds (1948), Reinhold Publication 00., pp.

- 58, 606 and 609. 

